Synthesis, chromatographic purification, and analysis of isomers of biliverdin IX and bilirubin IX
✍ Scribed by Karel P.M. Heirwegh; Norbert Blanckaert; Gustaaf Van Hees
- Book ID
- 102986463
- Publisher
- Elsevier Science
- Year
- 1991
- Tongue
- English
- Weight
- 699 KB
- Volume
- 195
- Category
- Article
- ISSN
- 0003-2697
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✦ Synopsis
Neutral solvent systems were developed to isolate the alpha, beta, gamma, and delta isomers of biliverdin IX dimethyl ester by TLC. The individual free acids of biliverdin IX were obtained by saponification of the corresponding dimethyl esters. The bilirubin IX isomers were prepared by reducing the corresponding biliverdin IX isomers with NaBH3CN. Starting from a pure biliverdin IX dimethyl ester, the corresponding free acid of biliverdin IX or bilirubin IX was available within 3-4 h. Preparation of spectrally pure bile pigment required final TLC on acid-cleaned neutral TLC plates. The absorption spectra of the free acids and dimethyl esters of biliverdin IX in methanol showed a broad band at about 650 nm and a sharp band at about 375 nm. The long-wave-length band was extremely sensitive to the presence of strong acid. A 10-fold molar excess of HCl caused a 35- to 50-nm shift of the absorption maximum to longer wavelengths and near doubling of the maximum absorption. The molar absorption coefficients of biliverdins were identical for each free acid and dimethyl ester pair. In each case, Beer's law was followed in both methanol and acidified methanol. Methanol also proved to be a suitable solvent for spectroscopic determination of the non-alpha isomers of bilirubin IX. The wavelength of maximum absorption and molar absorption coefficient of each dipyrrolic ethyl anthranilate azo pigment derived from the various bilirubin IX isomers are also reported.
📜 SIMILAR VOLUMES
## Abstract The three structural isomers bilirubin IXα (**1a**), IIIα (**2a**), and XIIIα (**3a**) have been separated on a preparative scale by high‐performance low‐pressure liquid chromatography. They were converted into their dimethyl esters **1b, 2b**, and **3b** and characterized by UV, IR, MS
## Abstract The total synthesis of [10‐^13^C]bilirubin IXα, the principal waste product of haem degradation, is described. Site specific labelling was accomplished by the Vilsmeier formylation of one of the dipyrrolic fragments using [1‐^13^C]dimethylformamide. The penultimate dehydrohalogenation r